This chapter offers a historical narrative of the co-evolution of digital media and civil society and provides insights into the implications of changes in the media environment for the realm of politics and the transformation of civil society activism in Southeast Asia. Covering three chronological but overlapping periods spanning from the 1990s to the early 2020s, it presents a historical periodisation that follows technological shifts – notably from the static Internet to blogging to social media – and the political ramifications of these shifts in civil society activism. The chapter highlights the ambivalent role of digital media as space and platform for civic engagement and mobilisation and as an exponent of polarisation, radicalisation, and manipulation.